Amines 4-methoxy-benzyl - amine

Reaction of A,A-dimcthylsullamoyl aziridines 323 and 325 with primary amines furnishes substituted 1,2,5-thiadiazolidine 1,1-dioxides 324 and 326, respectively, in a regioselective manner <06SL833>. Aziridine 325 is made from ( I /t,6,S ,Z)-bicyclo[4.2. l]non-3-en-9-one in two steps /V,/V-dimethylsulfamoyl imine formation using dimethylsulfamide and subsequent reaction with trimethylsulfoxonium ylide. The product from the reaction with 4-methoxy-benzyl amine can be subsequently manipulated (debenzylation and derivatization) to give the alternative nitrogen substitution pattern in a controlled manner. 

Dimethyl-propyl-amin Dicthyl-(2-phenyl-ethyl)-amin Benzyl-dime thyl-amin Dimethyl-(4-methoxy-benzyl)-amin Bcnz°L ... 

Recently, Backvall et al. reported that a p-methoxy derivative of dirutheitium complex 1 racemizes benzyl amines at 90-100°C in toluene and the DKRs using it were achieved successfully (Scheme 5). More than ten benzylic amines were transformed to the corresponding amides with good yields and high ee. ... 

Durch Ruthenium-katalysierte Oxidation sind neben N-Acyl-N-allyl-aminen (s. Bd. E5, S. 557, 1985) auch Acyl-aryl-amine zu a-Aminosauren oxidierbar, z. B. (5)-2-Deutero-glycin aus N-(a-Deutero-4-methoxy-benzyl)-carbamidsaure-tert.-butylester (1), 54% . Das (R)-2-Deutero-glycin (80%) wird durch Ozonolyse von (/ )-Deutero-(2-furyl)-phthalimido-methan (II) erhalten6 (S. 644). 

CI.AISI. N RF.ARRANGEMENT Benzyl-amine. Bis(benzonitrile)d ichlorupalla-dium(ll). Trimethyl 3-(methoxy)ortho-propionate. 

Benzyl groups are the second fiddles of the amine protection repertoire, and they are especially useful when a substrate is to be subjected to powerful orga-no metal lie reagents or metal hydrides which might attack a carbamate. Benzyl-amines are not generally cleaved by Lewis acids under preparatively useful conditions. The following discussion embraces benzylamines, diphenylmethylamines and their methoxy-substituted derivatives. 

Amin 4-Methoxy-benzyl- -Hydrochlorid E16d, 1161 (Hoffmann-Abbau)... 

Cyanamid [(4-Methoxy-benzyl-amino)-methylthio-methylen]-E4, 1298 [(RS)3C = N-CN + Amin]... 

Amin (4-Methoxy-benzyl)-nitro-propyl- EI6a, 1161 (N-Alkylier.) Benzoesaure 4-Amino-2-hydroxy- -(2-dimethylamino-ethylester) Vl/lc, 403... 

Ethan l-Benzoylamino-l-(5-methyl-2-oxo-l, 3-oxazolidino)- E14a/3, 606(En-amin + Ar—CO —NH2) Imidazol 5,5-Dimethyl-4-(4-methoxy-benzyl)-2-oxo-2,5-dihydro- -3-oxid E14b, 1432 (Amin-Oxin/COCl2)... 

In the same way, direct comparison with other groups15 shows that the simple methoxy director is less powerful than a sulfonamide 81 or a benzylic amine 82, but more powerful than F, CF3, NR2, or (CH2)2NR2. 

Nitro-benzaldehyd (4-Methoxy-benzyl)-(4-nitro-benzyl)-amin — 35% 4-Methoxy-benzaldehyd... 

Dimethyl-(4-mcthoxy-benzyl)-amin — 4-Methoxy-benzaldehyd 46%... 

Tris-[2-methyl-propyl]-amin(neutral) Benzyl-dimethyl-amin (pH 10,3) Bis-[3,4-mcthylendioxy-benzyl]-me-thyl-amin (50% H2S04) Dibenzyl-(4-methoxy-benzyl)-amin (50% H2S04)... 

In 2001, Funk reported a synthesis of ( )-FR901483 using an approach very different from those described previously, taking advantage of his amidoacrolein cycloaddition methodology to prepare 1 -alkyl-1 -aminocyclohexane derivatives, starting the synthesis from acyclic compounds. Moreover, Funk neither uses tyrosine derivatives nor needs an inversion at C(9) to install the phosphate unit. In Funk s retro synthetic analysis, shown in Scheme 23, he envisaged that lactam 60 possessed the necessary functionality for the introduction of the C(6) p-methoxy benzyl and C(3) methylamino substituents via enolate alkylation and amination reactions, respectively. 

Pyridinium salts, l-aryl-4-methoxy-2,6-dimethyl-synthesis, 3, 762 Pyridinium salts, N-aryloxy-rearrangements, 2, 354 Pyridinium salts, 1-benzyl-covalent amination, 2, 239 Pyridinium salts, N-benzyl-reactions... 

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